Let's rethink email

I've been using email longer than most people (more than a quarter of a century), so I think I have the credibility to say it's overdue for an overhaul.

Email as we know it has considerable security holes. And of course we're all sick of the straight-from-Satan's-lair spam. But let's not overlook how inherently inefficient it is. Once a boon to businesses, email has developed the annoying habit of burying information. It does this by piling up messages in threads; what you need to find is somewhere among the 30, 40 or 50 threads in a single email file, but who has the time to comb through them all to find that one essential nugget of data? We all know how this happens. Let's say eight people need to agree on a meeting time. The emails come into the thread one after another as the time is negotiated. In the end, perhaps 97% of the messages are irrelevant, but there they all are.

Way, way back (I already said I've been using email for a long time), Lotus Notes avoided this problem to a certain extent. Everyone in an email chain was referred to a linked file, and that one message was constantly updated.

Here's another shortcoming of email as we know it: It's next to impossible to retrieve a message that you wish you hadn't sent. Maybe you got more up-to-date information shortly after you sent the email, maybe you sent it to the wrong person, or maybe you simply said something you shouldn't have. I mean, who hasn't sobered up and realized that offering the CEO a candid assessment of his toupee was just a bad idea? If the recipient is using a POP3 email system, you can pretty much forget it, because everything is downloaded locally and is no longer influenced by changes to the server. But even when that's not the case, you're not likely to have any luck with an email recall attempt. And if you try, the recipient is probably going to know about it, and so your plan will backfire as the recipient will suddenly take an intense interest in what you so very much want to take back. (A very crafty PR person told me once that she would try to retrieve from reporters' inboxes a news release she had sent them, not because she thought she could get it back, but because she figured that would entice them to read it carefully. She understood her prey far too well.)

Now, as it happens, there's a company that is promising to relieve both of these problems. It says its system makes emails easily retrievable, even after the recipient has read it, and even if the recipient is on POP3. Seeing is believing, says I, so the company, called Criptext, sent me an email and I opened it. Five minutes later, I was told to try looking at it again. Wonders of wonders, I couldn't. OK, I thought, these guys may be on to something.

Criptext's approach is essentially to stream your email contents to you. The message looks like a regular email message (well, almost; more on that in a moment), but it is not really on your machine. The message holder is there, but the contents are streamed from Criptext's server. Because of this, there's a split-second delay when you open a message before the contents are displayed. It's not noticeable unless you're looking for it.

What this means is that you could look at that same message 50 times, and it might say different things each time, as the sender updates the file on the server. So as you and those seven other people negotiate that meeting time, the email message is constantly updated. You can leave the history intact, which is helpful as you try to coordinate a day and time when everyone is available, but once you've zeroed in on a time that works for everyone, you can zap the history and just send out the final, truly relevant information.

Oh, an aside: this system automatically encrypts all messages and all attachments -- using a private AES 512 bit encryption key -- and will decrypt it for anyone you send it to. (I wonder whether Hillary Clinton could have benefited from that?) According to Criptext CEO Mayer Mizrachi, "The server then shares a public RSA 2,048-bit encryption key with the user, which is used to securely transfer the unique AES 512 encryption key that encrypted the email to begin with. The email then safely reaches the user's unique box in the Criptext server."

Being able to seamlessly have all of your employees encrypting every message and attachment is compelling. Preliminary pricing from the company seems odd in that it wants to charge $50/month for "enterprises," with unlimited encrypted emails, but it doesn't define an enterprise. (Go for it, Walmart. That's quite a deal.)

The current beta-test version of the product, which I've played around with, has some logistical hurdles, but the concept is quite intriguing. Hurdle No. 1: Remember when I said it looks almost like every other message? It turns out that it's not text at all, but an image. That's a problem when you want to copy a line and use it in a document or drop some numbers into a spreadsheet. It's especially a problem when replying to a message and trying to comment on specific parts of the initial message.

Hurdle No. 2: The same capability that can make it convenient for the recipient and secure for the sender also makes it problematic for record-keeping. When you receive that final version of an important contract or a summary of what a colleague promises to deliver by next Thursday, you really want to save it and know that the sender won't be able to surreptitiously change the details. ("What are you talking about, Phil? I said I would only send you two models at that price and the rest were for 100 times that amount. Go back and reread what I sent you last week.")

There are easy fixes to these problems, Mizrachi said, and his team is exploring scenarios where one button would give a user the option to save that image file on the user's computer (smartphones, too) where it would be out of reach and, therefore, a permanent record of the discussion. A second button would allow the recipient to download a text version of the message. Although this would obliterate the security (a pop-up window or dialogue box would remind the recipient of that fact), it would make the contents fully usable, for commenting, spreadsheets, documents or anything else.

This is all happening at a point when companies (such as Microsoft) are scrambling to stay ahead of government subpoenas for email copies, while others (hello, Amazon) want to make sure that they preserve the right to peek and leverage your emails. So, yeah, it might be time indeed to rethink how corporate email is handled, and here's one company that's doing just that. I'll be interested to see if other new ideas follow.

Evan Schumanhas covered IT issues for a lot longer than he'll ever admit. The founding editor of retail technology site StorefrontBacktalk, he's been a columnist for CBSNews.com, RetailWeek and eWeek. Evan can be reached at eschuman@thecontentfirm.com and he can be followed at twitter.com/eschuman. Look for his column every other Tuesday.

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